O-Methylhydroxylamine hydrochloride → 1-(4-{3-[2,6-dichloro-4-(3,3-dichloro-allyloxy)-phenoxy]-propoxy}-phenyl)-propane-1,2-dione bis-(O-methyl-oxime)

HRID 2099933Notes

Reaction equation

HRID 2099933 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][CH2:17][O:18][C:19]2[C:24]([Cl:25])=[CH:23][C:22]([O:26][CH2:27][CH:28]=[C:29]([Cl:31])[Cl:30])=[CH:21][C:20]=2[Cl:32])=[CH:10][CH:9]=1)[C:5](=O)[CH3:6].Cl.[CH3:34][O:35][NH2:36]>N1C=CC=CC=1>[CH3:1][O:2][N:3]=[C:4]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][CH2:17][O:18][C:19]2[C:20]([Cl:32])=[CH:21][C:22]([O:26][CH2:27][CH:28]=[C:29]([Cl:30])[Cl:31])=[CH:23][C:24]=2[Cl:25])=[CH:10][CH:9]=1)[C:5](=[N:36][O:35][CH3:34])[CH3:6]

Participants

4

Reactant 2

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 766082031-(4-{3-[2,6-dichloro-4-(3,3-dichloro-allyloxy)-phenoxy]-propoxy}-phenyl)-propane-1,2-dione 1-(O-methyl-oxime)

Product 1

HCID 766082071-(4-{3-[2,6-dichloro-4-(3,3-dichloro-allyloxy)-phenoxy]-propoxy}-phenyl)-propane-1,2-dione bis-(O-methyl-oxime)

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

0.23 g of 1-(4-{3-[2,6-dichloro-4-(3,3-dichloro-allyloxy)-phenoxy]-propoxy}-phenyl)-propane-1,2-dione 1-(O-methyl-oxime) and 44 mg of O-methylhydroxylamine hydrochloride are stirred in 5 ml of pyridine at 80° C. for 2 hours. The reaction mixture is concentrated; the residue is taken up in ethyl acetate and washed with water. After concentration of the organic phase and purification over silica gel, the title compound is obtained. 1H-NMR (CDCl3) 300 MHz: 2.12 (s, 3H), 2.30 (m, 2H), 3.88 (s, 3H), 3.94 (s, 3H), 4.17 (t, 2H), 4.29 (t, 2H), 4.59 (d, 2H), 6.11 (t, 1H), 6.83 (s, 2H), 6.91 (d, 2H), 7.29 (d, 2H)

Workup

  1. concentrationThe reaction mixture is concentrated
  2. washwashed with water
  3. customAfter concentration of the organic phase and purification over silica gel

Sources & evidence

ORD record
ord-f1adf9eb30bc45c2abcaa7b00af1bec9
Source dataset
uspto-grants-2009_08
Patent number
US07569727B2

Reaction notes

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